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The Strathprints institutional repository is a digital archive of University of Strathclyde research outputs.

Strathprints serves world leading Open Access research by the University of Strathclyde, including research by the Strathclyde Institute of Pharmacy and Biomedical Sciences (SIPBS), where research centres such as the Industrial Biotechnology Innovation Centre (IBioIC), the Cancer Research UK Formulation Unit, SeaBioTech and the Centre for Biophotonics are based.

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Distamycin Analogues with Enhanced Lipophilicity: Synthesis and Antimicrobial Activity

Khalaf, A.I. and Waigh, R.D. and Drummond, A.J. and Pringle, B. and McGroarty, I. and Skellern, G.G. and Suckling, C.J. (2004) Distamycin Analogues with Enhanced Lipophilicity: Synthesis and Antimicrobial Activity. Journal of Medicinal Chemistry, 47 (8). pp. 2133-2156. ISSN 0022-2623

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Abstract

Forty-eight heterocyclic amino acid trimers, analogues of distamycin, with a number of features that enhance lipophilicity are described. They contain alkyl or cycloalkyl groups larger than methyl; some are N-terminated by acetamide or methoxybenzamide and are C-terminated by dimethylaminopropyl or aliphatic heterocylic aminopropyl substituents. The ability of these compounds to bind principally to AT tracts of DNA has been evaluated using capillary zone electrophoresis. Significant antimicrobial activity against key organisms such as MRSA and Candida albicans is shown by several compounds, especially those containing a thiazole. Moreover, these compounds have low toxicity with respect to several mammalian cell lines.